Green-blue dyestuffs of the triphenylmethane series, fast to alkali



Patented Aug. 18, 1925.

UNITED STATES mcnann onsrno AND m' nonr nnrnnn ASSIGNORS T0 CHEMIBCHEFADE-1K GREISHEIM-ELEK PATENT OFFICE.

, 0F OFFENBACH-ON-THE-MAIN, GERMANY.

'rRoN, or FRANKFURT-0N5 ran-mam, GM, 11 oonrona rxon.

GREEN-BLUE DYESTUFFS O15 THE TBIPHENYLME'IHANE SERIES, FAST T0 ALKALI.

Ho Drawing.

if) "t 11.141 J [[(h- Rpm-l) v i wherein a: and", represent-numbers lessthan 3, which dyestuffs are, when dry blue pow deis of avinetalliclustre, soluble in water to a beautiful-blue solution. The new dyestuflsmay be obtained 5 proportion of ortlzq-suliobenzaldehyfde with twomolecular 'roportio'ns of alkylbenzyl arvlamins,:whic are substituted inthe benzyl residue By halogens, particularly by chlorine and sulfonicgroups, and by oxidizing subsequently the products of condensation.Assuch alkylbenz larylamins, where on sulfonating the sul onic grou s-enter in the benzylresidue, may be u' ortho-, meta-,para-chlorobenzylethylanilin, 2.4-- and 2.6-

- di'chlorobenzylethylanilin. In the same man.

nor the bromated derivatives and the derivatives of: henzylmethylan'ilinmay be used.

Dyestufl's of the present type, but not concondensing one molecular'Applieation filed Kay 22, 1925. Serial 110.82, 184.

taining halogen atoms, are already known, the. new halogenated d estulfsare distinguished from the not he ogenated especially y the purity ofthe shade.

The following examples illustrate the nature of the invention, the partsbeingihy weight: A 1 Example I.

Ortho-chlorobenzylethylanilin, which is Obtained in the usual mannerfrom orthochlorobenzylchloride and monoethyla'nilin, is sulfonated bydissolving one art of the base in one to two parts of su furic acid,monohydrated acid, and stirring, Whilecold, with two equivalents of SO,in the form of oleum, until solubility in alkali has taken place. Inthis manner one sulfonic grou enters in the benzylresid'ue. The new sufonic acid forms a white powder, very little soluble in water, easilysoluble in alk'a'lies.

parts of the 'sulfonic acid are boiled with 23 parts ofortho-sulfobenzaldehyde (of 9fi er centstrength) in a uecus solution for2% ours under reflux'an the leuco-acid, thus obtained, is oxidized inacid solution with peroxid of lead into the dyestufl.

The lead being separated, the dyestutf liavin' in the form of the freeacid prob- .ably t e formula:

CgH H on. li n,

' N o l is salted out and dried. It dyes wool in blue shades of anespecial purity and clearness, the dye-bath being more exhausted thanthe cl e-bath of the corresponding dyestufl', whic is free of chlorine.In the same manner by startin from metaand parachlorosulfobenzyletylanilin, also white powders, very little soluble in water and easilysoluble in alkalies, the corresponding dyestuffs are obtained, havingthe same valuable properties.

Example 2.

Starting from 2.6-dichlorobenz lethylanilin and using 72 parts of the sufonic acid for condensing with 23 parts of ortho-sulfobenzaldehydc,according to the same method a dyestufi' is obtained dyeing wool in alittle more greenish blue shade of an especial purity and olearness.

In the same manner the sulfonic'acid of 2.4-dichlorobenzylethylanilinmay be used.

All the mentioned sulfonic acids have the same aspect and the sameproperties.

Now what we claim and desire to secure by Letters Patent .is thefollowing:

1. As new compounds green-blue dyestuffs of the triphenylmethan series,fast to alkali, which are sulfonated and. halogenated derivatives ofdibenzyl-dialkyl-diaminotriphenylmethan -'ortho sulfonic acid,corresponding ixrthe state of the free acids probably to the generalformula:

2. As new compounds green-blue dyestulls' of the triphenylmethan-serics,fast to alkali, which are sulfonated and chlorinated derivatives of thedibenzyl-dialkyldiamino-triphenylmethan ortho sulfonic acid,corresponding probably in the state of the free acids to the generalformula:

wherein n represent'a number less than 3, which dyestuffs are when dryblue powders of a metallic lustre, soluble in watento a beautiful bluesolution and dyeing wool in especially pure and clear shades, whichdyestufi's may be obtained by condensing one molecular proportion ofortho-sulfobenzalde-. hyde with --two molecular proportions ofalkylbenzylarylamins, which are substituted in the benzyl residue bychlorine and sulfonicgroups, and by oxidizing subsequently the productsof condensation.

3. As new compound a green-blue dyestntfv of the triphenylniethanseries, fast to alkali, having in the state of the free acid probablythe formula:

on on, L In,

which dyestufi' is when dry a blue powder of a metallic lustre, solublein water to a beautiful blue solution and dyeing wool in especially pureand clear shades, which dyestutf may be obtained by condensing onemolecular roportion of ortho-sulfobenzaldchyde wit ii two molecularproportions of ortho chlorosulfobcnzylcthylanilin and by oxidizingsubsequently the product of condcnsation.

In testimony, that we claim the foregoing as our invention, we havesigned our names, this 11th dayvot May 1925.

RICHARD GESING. RUDOLF REYHER.

dyestuffs are obtained, having the same valuable properties.

Example 2.

Starting from 2.6-dichlorobenzylethylanilin and using 72 arts of the sufonic-acid for condensing with 23 parts of ortho-sulfobenzaldchyde,accordin to the same method a dyestufi' is obtained dyeing Wool in alittle more greenish blue shade of an especial purity and clearness.

In the same manner the sulfonic acid of 2.4-dichlorobenaylethylanilinmay be used. All the mentioned sulfonic acids have the same aspect andthe same properties.

Now what we claim and desire to secure by Letters Patent is thefollowing:

1. As new compounds green-blue dyestuffs of the triphenylmethan series.fast to alkali, which are sulfonated and halogenated derivatives ofdibenzyl-dialkyl-diaminotriphenylmethan ortho sulfonic acid,corresponding in the state of the free acids prob ably to the generalformula:

2. As new compounds green-blue dyestutl's of the triphenylmetban-series,fast to alkali, which are sulfonated and chlorinated derivatives of thedibenzyl-dialkyldiamino-triphenylmethan ortho sulfonic acid,corresponding probably in the state of the free acids to the generalformula:

alkv] lk 1 N 0H N Y on, H,

[ t-n) t-n) 501K 0311 OIH wherein n re resent/a number less than 3,which dyestu s are when dry blue powders of a metallic lustre, solublein water to a beautiful blue solution and dyeing wool in especially pureand clear shades, which dyestutl's may be obtained by condensing onemolecular proportion of ortho-sulfobenzalde hydc with two molecularproportions of a'lkylbenzylarylamins, which are substituted in thebenzyl residue by chlorine and sulfonic groups, and by oxidizingsubsequently the products of condensation.

3. As new compound a green-blue dyestufi' of the triphenylmethan series,fast to alkali, having in the state of the free acid probably theformula:

N on N (Ha O L G 01 which dyestufi' is when dr a blue powder of ametallic lustre, solub e in water to a beautiful blue solution anddyeing wool in especially pure and clear shades, which dye- CgH; I

stuff may be obtained by condensing one Certificate of Correction.

It is hereby certified that the name of the assignee in Letters PatentNo. 1,550,534, fiigmted Au ust 18, 1925, u on the application of RichardGesing and Rudolf yher, of

fl'enbach-on-theain, Germany, for an improvement in Green-Blue Dyestuffsof the Tri henyhnethane Series, Fast to Alkali, was erroneously writtenand printed as Chemisc he Fabrik Greisheim-Elektron, whereas saidprinted as Ghemische-Fab'r'ik Grieakeim-Elektron.

should have been written and as shown by the records of assignments inthis office;- and that the said Letters Patent should be read with thiscorrection therein that the same may conform to the record of the casein the'Patent Oflice.

Signed and sealed this 3d day of November, A. D. 1925.

[emu] KARL FENNING, Acting Gan missions?" of Patents.

Certificate of Correction.

It is hereby certified that the name of the assignee in Letters PatentNo. 1,550,534. rranted Au ust 18, 1925, upon the application of Richard(lesing and Rudolf yher, of gfl'enbach-on-the-Main, Gernmny. for animprovement in Green-Blue Dyestufi's of the Triphenyhnethane Series,Fast t0 Alkali, was erroneously written and printed as Chemische FabrikGreisheim-l llektron, whereas said name should have been written andprinted as Cltemische-Fabrik GM-sbeirn-E/dutro'n.

as shown by the records of assignments in this office; and that the saidLetters Patent should he read with this correction therein that the samemay conform to the record of the case in the Patent Office.

Signed and sealed this 3d day of November, A. D. 1925.

[SEAL] KARL FENNING,

Acting Con 'wissioner of Patents.

